128146-20-3Relevant academic research and scientific papers
Peroxonium Ions from Butyl β-Iodoalkyl Peroxides: An Investigation of the Effect of Replacing tert-Butyl by sec-Butyl and n-Butyl
Bloodworth, A. J.,Khalaf, Yasmin S.,Mitchell, John C.,Spencer, Michael D.
, p. 265 - 278 (2007/10/02)
β-Iodoalkyl peroxides, PhCH2CMe(OOC4H9)CH2I where C4H9 = n-butyl and sec-butyl, react with silver trifluoroacetate to afford peroxy-migrated substitution products PhCH2CMe(OCOCF3)CH2OOC4H9 and peroxy-migrated elimination products CH2=C(CH2Ph)CH2OOC4H9 and PhCH=C(CH3)CH2OOC4H9 similar to those previously obtained for the tert-butyl compound. threo-3-n-Butylperoxy-2-iodopentane, MeCH(I)CH(OO-n-Bu)Et, reacts with silver trifluoroacetate to give two regioisomeric substitution products whereas erythro-2-n-butylperoxy-3-iodopentane, MeCH(OO-n-Bu)CH(I)Et affords only one trifluoroacetate, again parallel to the behaviour of the corresponding tert-butyl compounds.MINDO/3 calculations of the lowest energy conformations of n-butylated and tert-butylated perepoxides derived from pent-2-ene place the butyl groups away from the threemembered ring.An earlier interpretation of the tert-butyl results is modified in the light of these findings.
